Harmal 1

Harmal

Harmal

Harmal (Peganum harmala) flower

Scientific classification

Kingdom: Plantae Unranked: Angiosperms Unranked: Eudicots Unranked: Rosids Order: Sapindales Family: Nitrariaceae Genus: Peganum

Species: P. harmala

Binomial name

Peganum harmalaL.[1]

Harmal seed capsules

Harmal (Peganum harmala) is a plant of the familyNitrariaceae, native from the eastern Mediterraneanregion east to India. It is also known as Wild Rue orSyrian Rue because of its resemblance to plants of therue family.

It is a perennial plant which can grow to about 0.8 mtall,[2] but normally it is about 0.3 m tall.[3] The roots ofthe plant can reach a depth of up to 6.1 m, if the soil itis growing in is very dry.[3] It blossoms between Juneand August in the Northern Hemisphere.[4] The flowersare white and are about 2.5–3.8 cm in diameter.[4] Theround seed capsules measure about 1–1.5 cm indiameter,[5] have three chambers and carry more than50 seeds.[4]

Peganum harmala was first planted in the United States in 1928 in the state of New Mexico by a farmer wanting tomanufacture the dye "Turkish Red" from its seeds.[3] Since then it has spread invasively to Arizona,

Harmal 2

Peganum harmala seeds

California, Montana, Nevada, Oregon, Texas andWashington.[6] "Because it is so drought tolerant,African rue can displace the native saltbushes andgrasses growing in the salt-desert shrub lands of theWestern U.S."[3]

Common names:[7]

• African rue• Esphand (Persian, دنپس - دنپسا)• Harmal peganum• Harmal shrub• Harmel

• Isband• Ozallaik• Peganum• Steppenraute• Syrian rue• Yüzerlik, üzerlik (Turkish)• Üzərlik• Luotuo-peng (Chinese, 骆驼篷)

Traditional usesIn Turkey Peganum harmala is called yüzerlik or üzerlik. Dried capsules from this plant are strung and hung inhomes or vehicles to protect against "the evil eye."

Peganum harmala seeds heated over a gas flame as incense

In Afghanistan, Azerbaijan, Iran, Iraq, Turkey,Uzbekistan and Tajikistan, dried capsules (known inPersian as دنپسا espænd or هناددنفسا esfænd-dānehand испанд ispand or испандут ispandut by Tajiksand Bukharian Jews of Central Asia) mixed with otheringredients are placed onto red hot charcoal,[8] wherethey explode with little popping noises, releasing afragrant smoke that is wafted around the head of thoseafflicted by or exposed to the gaze of strangers. As thisis done, an ancient prayer is recited. This prayer is saidby Jews (more specifically, Bukharian Jews) andMuslims as well as by Zoroastrians. This Persianpractice dates to pre-Islamic, Zoroastrian times. In Iran,this ritual is sometimes performed in traditional restaurants, where customers are exposed to the eyes of strangers.

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Syrian Rue

Peganum harmala fruit

Harmal 4

Peganum harmala seeds as sold in a Middle Eastern foods grocerystore

Harmal has been used as an entheogen in the MiddleEast, and in modern Western culture, it is often used asan analogue of Banisteriopsis caapi to create an ad hocAyahuasca, the South American mixture ofphytoindoles including DMT with β-carbolines.However, Harmal has distinct aspects from caapi and aunique entheogenic signature. Some scholars identifyHarmal with the entheogenic haoma of pre-ZoroastrianPersian religions.[9]

A red dye, "Turkey Red,"[3] from the seeds is oftenused in Western Asia to dye carpets.[10] It is also usedto dye wool.[3] When the seeds are extracted withwater, a yellow fluorescent dye is obtained.[11] If theyare extracted with alcohol, a red dye is obtained.[11]

The stems, roots and seeds can be used to make inks,stains and tattoos.[12]

Medicinal uses

Peganum harmala is used as an analgesic andantiinflammatory agent.[13]

In Yemen it was used to treat depression,[14] and it hasbeen established in the laboratory that harmaline, an active ingredient in Peganum harmala, is a central nervoussystem stimulant and a "reversible inhibitor of MAO-A (RIMA),"[15] a category of antidepressant.

Peganum harmala

Smoke from the seeds kills algae, bacteria, intestinalparasites and molds.[10] Peganum harmala has"antibacterial activity,"[16] including antibacterialactivity against drug-resistant bacteria.[17]

The "root is applied to kill lice" and when burned, theseeds kill insects.[18] It also inhibits the reproduction ofthe Tribolium castaneum beetle.[19]

It is also used as an anthelmintic (to expel parasiticworms).[18] Reportedly the ancient Greeks usedpowdered Peganum harmala seeds to get rid oftapeworms and to treat recurring fevers (possiblymalaria).[20]

Peganum harmala is an abortifacient,[21] and, in largequantities, it can reduce spermatogenesis and male fertility in rats.[22]

Harmal 5

Antiprotozoal

Harmine, a compound present in Peganum harmala, fluoresces underultraviolet light

It is fairly effective against protozoa including malaria.There is evidence that it may be effective againstdrug-resistant protozoa.[17] It is given in a decoction forlaryngitis.[18]

One of the compounds found in Peganum harmala,vasicine (peganine) has been found to be safe andeffective against Leishmania donovani, a protozoanparasite that can cause potentially "fatal visceralleishmaniasis."[23] "Peganine hydrochloride dihydrate,besides being safe, was found to induce apoptosis inboth the stages of L. donovani via loss of mitochondrialtransmembrane potential."[24]

Another alkaloid harmine found in Peganum harmala,". . .because of its appreciable efficacy in destroyingintracellular parasites as well as non-hepatotoxic and non-nephrotoxic nature, harmine, in the vesicular forms, maybe considered for clinical application in humans."[25]

One study using the medicinal plant Peganum harmala showed it to have a lifesaving effect on cattle infected withthe protozoal East Coast fever,[26] which can be 100% fatal and killed 1.1 million cattle in Africa in 1992.

Anticancer"The beta-carboline alkaloids present in medicinal plants, such as Peganum harmala and Eurycoma longifolia, haverecently drawn attention due to their antitumor activities. Further mechanistic studies indicate that beta-carbolinederivatives inhibit DNA topoisomerases and interfere with DNA synthesis."[27]

Peganum harmala has antioxidant and antimutagenic properties.[28]

Peganum harmala as well as harmine exhibit cytotoxicity with regards to HL60 and K562 leukemia cell lines.[29]

Ground Peganum harmala seeds have been used occasionally to treat skin cancer and subcutaneous cancerstraditionally in Morocco.[30] Seed extracts also show effectiveness against various tumor cell lines both in vitro andin vivo.[30]

Alkaloids

Harmaline, one of the alkaloids of Peganumharmala

The active alkaloids of Harmal seeds are the MAOI-A (monoamineoxidase inhibitor A) compounds:

• Harmane, 0.16%[31]

• Harmine, 0.44[32] –1.84%[31] –4.3%[33]

The coatings of the seeds are said to contain large amounts ofharmine.[2]

• Harmaline, 0.25%[31] –0.79%[32] –5.6%[33]

• Harmalol, 0.6%[33] –3.90%[31]

• Tetrahydroharmine, 0.1%[33]

Total harmala alkaloids were at least 5.9% per dried weight, in one study.[31]

• Vasicine (peganine),[21] 0.25%[32]

Harmal 6

• Vasicinone,[21] 0.0007%[32]

Vasicine

The stems of the plant contain about 0.36% alkaloids, the leaves about0.52%,[34] and the roots up to 2.5%.[35]

Harmine and harmaline are reversible inhibitors of MAO-A (RIMA).[15]

References[1] "Peganum harmala information from NPGS/GRIN" (http:/ / www. ars-grin. gov/ cgi-bin/

npgs/ html/ taxon. pl?27098). . Retrieved 2008-02-17.

[2] "Peganum genus" (http:/ / www. cdfa. ca. gov/ phpps/ ipc/ weedinfo/ peganum. htm). www.cdfa.ca.gov. . Retrieved 2008-02-02.[3] "RECOGNITION AND CONTROL OF AFRICAN RUE IN NEVADA" (http:/ / 72. 14. 253. 104/ search?q=cache:sfvO8us46s8J:www.

unce. unr. edu/ publications/ files/ nr/ 2001/ FS0145. pdf+ "peganum+ harmala"+ "red+ dye"& hl=en& ct=clnk& cd=40& gl=us& ie=UTF-8).72.14.253.104. . Retrieved 2008-04-19.

[4] "Erowid Syrian Rue Vaults: Smoking Rue Extract / Harmala" (http:/ / www. erowid. org/ plants/ syrian_rue/ syrian_rue_info9. shtml).www.erowid.org. . Retrieved 2008-12-01.

[5] "Lycaeum > Leda > Peganum harmala" (http:/ / leda. lycaeum. org/ ?ID=360). leda.lycaeum.org. . Retrieved 2008-12-01.[6] "PLANTS Profile for Peganum harmala (harmal peganum) / USDA PLANTS" (http:/ / plants. usda. gov/ java/ profile?symbol=PEHA).

USDA. 2008-01-17. . Retrieved 2008-01-18.[7] "Catalogue of Life : 2007 Annual Checklist : Peganum harmala L." (http:/ / www. catalogueoflife. org/ show_species_details.

php?record_id=715140). Integrated Taxonomic Information System (ITIS). 2007-01-18. . Retrieved 2008-01-18.[8] "Aspand - Espand - Esfand - Esphand Against the Evil Eye in Zoroastrian Magic" (http:/ / www. luckymojo. com/ aspand. html). . Retrieved

2008-01-19.[9] Karel van der Torn, ed., "Haoma," Dictionary of Deities and Demons in the Bible. (New York: E.J. Brill, 1995), 730.[10] "Peganum harmala" (http:/ / www. ibiblio. org/ pfaf/ cgi-bin/ arr_html?Peganum+ harmala). www.ibiblio.org. . Retrieved 2008-03-18.[11] "Mordants" (http:/ / www. fortlewis. edu/ anthro/ ethnobotany/ Dbase/ images/ Documents/ SW_DYEPLANTS_2. htm).

www.fortlewis.edu. . Retrieved 2008-04-19.[12] "Aluka - Entry for Peganum harmala Linn. [family ZYGOPHYLLACEAE (http:/ / www. aluka. org/ action/ showMetadata?doi=10. 5555/

AL. AP. UPWTA. 5_608& pgs=& cookieSet=1)"]. www.aluka.org. . Retrieved 2008-03-18.[13] Monsef, Hamid Reza; Ali Ghobadi, Mehrdad Iranshahi, Mohammad Abdollahi (19 February 2004). "Antinociceptive effects of Peganum

harmala L. alkaloid extract on mouse formalin test" (http:/ / www. ualberta. ca/ ~csps/ JPPS7(1)/ M. Abdolahi/ peganum. pdf) (PDF). JPharm Pharmaceut Sci 7 (1): 65–9. . Retrieved 2008-02-02.

[14] "Moses the Shaman" (http:/ / www. scribd. com/ doc/ 2231000/ Moses-the-Shaman). www.scribd.com. . Retrieved 2008-03-17.[15] Massaro, Edward J. (2002). Handbook of Neurotoxicology (http:/ / books. google. com/ ?id=2c2K-epbCDQC& pg=PA237& lpg=PA237&

dq=harmaline+ antidepressant). Humana Press. p. 237. ISBN 0896037967. .[16] Prashanth, D.; S. John (26 March 1999). "Antibacterial activity of Peganum harmala" (http:/ / www. sciencedirect. com/

science?_ob=ArticleURL& _udi=B6VSC-3Y9HHY8-P& _user=10& _rdoc=1& _fmt=& _orig=search& _sort=d& view=c&_acct=C000050221& _version=1& _urlVersion=0& _userid=10& md5=aa590588ea25645b5368168a6ad4fcb8). Fitoterapia 70 (4): 438–9.doi:10.1016/S0367-326X(99)00065-9. . Retrieved 2008-02-02.

[17] Arshad N, Zitterl-Eglseer K, Hasnain S, Hess M (Nov 2008). "Effect of Peganum harmala or its beta-carboline alkaloids on certain antibioticresistant strains of bacteria and protozoa from poultry". Phytother Res 22 (11): 1533–8. doi:10.1002/ptr.2528. PMID 18814210.

[18] "Peganum harmala" (http:/ / www. sdpi. org/ alpine medicianl herbs/ 39. htm). 2004. . Retrieved 2008-02-02.[19] Jbilou R, Amri H, Bouayad N, Ghailani N, Ennabili A, Sayah F (Mar 2008). "Insecticidal effects of extracts of seven plant species on larval

development, alpha-amylase activity and offspring production of Tribolium castaneum (Herbst) (Insecta: Coleoptera: Tenebrionidae)".Bioresour Technol. 99 (5): 959–64. doi:10.1016/j.biortech.2007.03.017. PMID 17493805.

[20] Panda H (2000). Herbs Cultivation and Medicinal Uses (http:/ / books. google. com/ ?id=Hlh9o7XhesEC& pg=PA434& lpg=PA434&dq="peganum+ harmala"+ traditional+ uses). Delhi: National Institute Of Industrial Research. pp. 435. ISBN 8186623469. .

[21] www.thenook.org (http:/ / www. thenook. org/ archives/ tek/ 06332ott. html)[22] El-Dwairi QA, Banihani SM (Jun 2007). "Histo-functional effects of Peganum harmala on male rat's spermatogenesis and fertility". Neuro

Endocrinol Lett. 28 (3): 305–10. PMID 17627267.[23] Misra P, Khaliq T, Dixit A, et al. (Nov 2008). "Antileishmanial activity mediated by apoptosis and structure-based target study of peganine

hydrochloride dihydrate: an approach for rational drug design". J Antimicrob Chemother. 62 (5): 998–1002. doi:10.1093/jac/dkn319.PMID 18694906.

[24] Misra P. et al. (2008). "Antileishmanial activity mediated by apoptosis and structure-based target study of peganine hydrochloride dihydrate:an approach for rational drug design.". Journal of Antimicrobial Chemotherapy 62 (5): 998–1002. doi:10.1093/jac/dkn319. PMID 18694906.

[25] Lala S. et al. (2004). "Harmine: evaluation of its antileishmanial properties in various vesicular delivery systems.". Journal of DrugTargeting 12 (3): 165–75. doi:10.1080/10611860410001712696. PMID 15203896.

Harmal 7

[26] Derakhshanfar A, Mirzaei M (Mar 2008). "Effect of Peganum harmala (wild rue) extract on experimental ovine malignant theileriosis:pathological and parasitological findings". Onderstepoort J Vet Res. 75 (1): 67–72. PMID 18575066.

[27] Li Y, Liang F, Jiang W, et al. (Aug 2007). "DH334, a beta-carboline anti-cancer drug, inhibits the CDK activity of budding yeast" (http:/ /www. landesbioscience. com/ journals/ cbt/ abstract. php?id=4382). Cancer Biol Ther. 6 (8): 1193–9. PMID 17622795. .

[28] Moura DJ, Richter MF, Boeira JM, Pêgas Henriques JA, Saffi J (Jul 2007). "Antioxidant properties of beta-carboline alkaloids are related totheir antimutagenic and antigenotoxic activities". Mutagenesis 22 (4): 293–302. doi:10.1093/mutage/gem016. PMID 17545209.

[29] Jahaniani F, Ebrahimi SA, Rahbar-Roshandel N, Mahmoudian M (Jul 2005). "Xanthomicrol is the main cytotoxic component ofDracocephalum kotschyii and a potential anti-cancer agent". Phytochemistry 66 (13): 1581–92. doi:10.1016/j.phytochem.2005.04.035.PMID 15949825.

[30] Lamchouri, F; Settaf A, Cherrah Y, Zemzami M, Lyoussi B, Zaid A, Atif N, Hassar M (1999 Nov-Dec). "Antitumour principles fromPeganum harmala seeds". Thérapie 54 (6): 753–8. PMID 10709452.

[31] Hemmateenejad B, Abbaspour A, Maghami H, Miri R, Panjehshahin MR (Aug 2006). "Partial least squares-based multivariate spectralcalibration method for simultaneous determination of beta-carboline derivatives in Peganum harmala seed extracts". Anal Chim Acta 575 (2):290–9. doi:10.1016/j.aca.2006.05.093. PMID 17723604.

[32] Pulpati H, Biradar YS, Rajani M (2008). "High-performance thin-layer chromatography densitometric method for the quantification ofharmine, harmaline, vasicine, and vasicinone in Peganum harmala". J AOAC Int 91 (5): 1179–85. PMID 18980138.

[33] Herraiz T, González D, Ancín-Azpilicueta C, Arán VJ, Guillén H. (2010). "beta-Carboline alkaloids in Peganum harmala and inhibition ofhuman monoamine oxidase (MAO).". Food Chem Toxicol. 48 (3): 839–43. doi:10.1016/j.fct.2009.12.019. PMID 20036304.

[34] Hammiche, V.; R. Merad (November 1997). "Peganum harmala L. (PIM 402F, French)" (http:/ / www. inchem. org/ documents/ pims/plant/ pim402fr. htm) (in French). International Programme on Chemical Safety. . Retrieved 2008-01-19.

[35] "Steppenraute (Peganum harmala) im GIFTPFLANZEN.COMpendium - www.giftpflanzen.com" (http:/ / www. giftpflanzen. com/peganum_harmala. html). www.giftpflanzen.com. . Retrieved 2008-04-18.

Further reading• Al-Shamma A, Drake S, Flynn DL, et al. (1981). "Antimicrobial agents from higher plants. Antimicrobial agents

from Peganum harmala seeds". J Nat Prod. 44 (6): 745–7. doi:10.1021/np50018a025. PMID 7334386.

External links• Erowid Syrian Rue Vault (http:/ / www. erowid. org/ plants/ syrian_rue/ syrian_rue. shtml)• Peganum harmala (Plants for a Future Database) (http:/ / www. pfaf. org/ database/ plants. php?Peganum+

harmala)• Aspand (Peganum harmala Seeds Used in Religious Rite) (http:/ / www. luckymojo. com/ aspand. html)• Peganum harmala List of Chemicals (Dr. Duke's Databases) (http:/ / sun. ars-grin. gov:8080/ npgspub/ xsql/

duke/ plantdisp. xsql?taxon=706)• Peganum harmala (FAO — Food and Agriculture Organization of the United Nations) (http:/ / 193. 43. 36. 103/

ag/ AGP/ agpc/ doc/ Gbase/ new_species/ peghar. htm)

Article Sources and Contributors 8

Article Sources and ContributorsHarmal  Source: http://en.wikipedia.org/w/index.php?oldid=415651666  Contributors: ***Ria777, Ahabvihrea, ArmadilloFromHell, AxelBoldt, Barticus88, C4 Diesel, Cacycle, Cantor,Capricorn42, Chem-awb, Chris the speller, Coaster420, Ctesiphon7, DOSGuy, Dadonene89, Danelo, DanielCD, Darwinek, Ehsan soltani, Foolishben, Grinter, Gypsyleif, Heah, Hesperian,Hilarleo, Iridescent, Jasminek, JoJan, Kent, Leyo, MPF, Mani1, MrStalker, Nono64, Ogress, Psychonaught, RDBrown, Rich Farmbrough, Rjwilmsi, Ronz, Sneekyninja21,Someoneinmyheadbutit'snotme, Stemonitis, Tesscass, The Man in Question, U-571, Varlaam, Whig, WriterHound, 47 anonymous edits

Image Sources, Licenses and Contributorsfile:Peganum harmala1.jpg  Source: http://en.wikipedia.org/w/index.php?title=File:Peganum_harmala1.jpg  License: GNU Free Documentation License  Contributors: JoJan, Photohound,WayneRayImage:Peganum harmala0.jpg  Source: http://en.wikipedia.org/w/index.php?title=File:Peganum_harmala0.jpg  License: GNU Free Documentation License  Contributors: JoJan, PhotohoundImage:Peganum-harmala-seeds.jpg  Source: http://en.wikipedia.org/w/index.php?title=File:Peganum-harmala-seeds.jpg  License: unknown  Contributors: Kirkbride, J.H., Jr., C.R. Gunn, andM.J. Dallwitz. 2006.Image:Peganum-harmala-incense.jpg  Source: http://en.wikipedia.org/w/index.php?title=File:Peganum-harmala-incense.jpg  License: Creative Commons Attribution-Sharealike 3.0 Contributors: Nima Shafaieh -- هیئافش امین

Image:Syrian Rue Seeds.jpg  Source: http://en.wikipedia.org/w/index.php?title=File:Syrian_Rue_Seeds.jpg  License: Public Domain  Contributors: User:Coaster420Image:Peganum-harmala-fruit.jpg  Source: http://en.wikipedia.org/w/index.php?title=File:Peganum-harmala-fruit.jpg  License: unknown  Contributors: Kirkbride, J.H., Jr., C.R. Gunn, andM.J. Dallwitz. 2006.Image:Peganum-harmala-esphand-4oz.jpg  Source: http://en.wikipedia.org/w/index.php?title=File:Peganum-harmala-esphand-4oz.jpg  License: GNU Free Documentation License Contributors: CubicalmanImage:Peganum-harmala-nps.jpg  Source: http://en.wikipedia.org/w/index.php?title=File:Peganum-harmala-nps.jpg  License: unknown  Contributors: NPSFile:Harmaline Harmine.jpg  Source: http://en.wikipedia.org/w/index.php?title=File:Harmaline_Harmine.jpg  License: Public Domain  Contributors: User:Coaster420Image:Harmaline (small).svg  Source: http://en.wikipedia.org/w/index.php?title=File:Harmaline_(small).svg  License: Public Domain  Contributors: Original uploader was Eloil at en.wikipediaImage:Vasicine.png  Source: http://en.wikipedia.org/w/index.php?title=File:Vasicine.png  License: Public Domain  Contributors: User:Photohound

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